3,7-anhdyro-1,2,6-trideoxy-6-C-<3-hydroxy-<(1,1-dimethylpropyl)dimethylsilyl>ethynyl>-1-C-iodo-5,8-bis-O-(methoxymethyl)-4-O-(triisopropylsilyl)-D-glycero-D-gulo-oct-1-ynitol | 221663-13-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3,7-anhdyro-1,2,6-trideoxy-6-C-<3-hydroxy-<(1,1-dimethylpropyl)dimethylsilyl>ethynyl>-1-C-iodo-5,8-bis-O-(methoxymethyl)-4-O-(triisopropylsilyl)-D-glycero-D-gulo-oct-1-ynitol
• CAS: 221663-13-4
• 化学式: C₃₀H₅₅IO₇Si₂
• 分子量: 710.838
• InChiKey: UTBBWHXLOROBGO-ZCCUTQAASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.35
• 重原子数：
  40.0
• 可旋转键数：
  15.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.87
• 拓扑面积：
  75.61
• 氢给体数：
  1.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  3,7-anhdyro-1,2,6-trideoxy-6-C-<3-hydroxy-<(1,1-dimethylpropyl)dimethylsilyl>ethynyl>-1-C-iodo-5,8-bis-O-(methoxymethyl)-4-O-(triisopropylsilyl)-D-glycero-D-gulo-oct-1-ynitol 在 tris-(dibenzylideneacetone)dipalladium(0) 、 copper(l) iodide 、 P(fur)3 、 4-甲基苯磺酸吡啶 、 三乙胺 作用下， 以 二氯甲烷 、 二甲基亚砜 为溶剂， 反应 25.0h， 生成 5,9-anhdyro-1,2,3,4,8-pentadeoxy-8-C-<<<1,1-dimethyl-3-<(tetrahydro-2H-pyran-2-yl)oxy>propyl>dimethylsilyl>ethynyl>-7,10-bis-O-(methoxymethyl)-6-O-(triisopropylsilyl)-D-glycero-D-gulo-deca-1,3-diynitol-1-yl-(1->6-C)-3,7-anhydro-1,2,6-trideoxy-4-O-(tr...
  参考文献：
  名称：

  Oligosaccharide Analogues of Polysaccharides, Part 17, Synthesis and Characterization of a Hexadecamer: Evidence for the Essential Structural Role of the Intramolecular, Interresidue C(3)−OH⋅⋅⋅O−C(5) Hydrogen Bond in Celluloses

  摘要：

  The hexadecamer 63 dissolves readily in DMSO and shows no sign of association, in agreement with the essential structural role of the intramolecular, interresidue C(3)-OH ... O-C(5) H-bond of celluloses, MM3 Calculations predict a rod-like shape for the cello-oligosaccharides In agreement with this, nanocrystalline domains of parallel chains are observed by high-resolution electron microscopy (HREM) for 54 and 63 on carbon-coated copper grids. For the synthesis of the hexadecamer 54, we studied the influence of protecting groups on the cross-coupling of acetyleno-oligosaccharides and on their solubility (Scheme 2). The octamer 12 derived from the minimally O-protected monomer 2 is insoluble, while the methoxymethyl- and triisopropysilyl-protected hexadecamer 54 prepared in twelve steps from the dimer 41 (Scheme 4), is readily soluble in a variety of solvents. O- and C-deprotection of 54 led in four steps and in 76% yield to the hexadecamer 63 (Schemes 5 and 6). There is only a small difference of spectroscopic properties between the protected octamer 50 and hexadecamer 54, and, similarly, between the unprotected octamer 64 and hexadecamer 63 (Fig. 3).

  DOI：

  10.1002/(sici)1522-2675(19990210)82:2<198::aid-hlca198>3.0.co;2-y
• 作为产物：
  描述：

  3,7-anhdyro-1,2,6-trideoxy-1-C-iodo-5,8-bis-O-(methoxymethyl)-6-C-<<<1,1-dimethyl-3-<(triisopropylsilyl)oxy>propyl>dimethylsilyl>ethynyl>-4-O-(triisopropylsilyl)-D-glycero-D-gulo-oct-1-ynitol 在 盐酸 作用下， 以 乙醇 为溶剂， 反应 14.0h， 以96%的产率得到3,7-anhdyro-1,2,6-trideoxy-6-C-<3-hydroxy-<(1,1-dimethylpropyl)dimethylsilyl>ethynyl>-1-C-iodo-5,8-bis-O-(methoxymethyl)-4-O-(triisopropylsilyl)-D-glycero-D-gulo-oct-1-ynitol
  参考文献：
  名称：

  Oligosaccharide Analogues of Polysaccharides, Part 17, Synthesis and Characterization of a Hexadecamer: Evidence for the Essential Structural Role of the Intramolecular, Interresidue C(3)−OH⋅⋅⋅O−C(5) Hydrogen Bond in Celluloses

  摘要：

  The hexadecamer 63 dissolves readily in DMSO and shows no sign of association, in agreement with the essential structural role of the intramolecular, interresidue C(3)-OH ... O-C(5) H-bond of celluloses, MM3 Calculations predict a rod-like shape for the cello-oligosaccharides In agreement with this, nanocrystalline domains of parallel chains are observed by high-resolution electron microscopy (HREM) for 54 and 63 on carbon-coated copper grids. For the synthesis of the hexadecamer 54, we studied the influence of protecting groups on the cross-coupling of acetyleno-oligosaccharides and on their solubility (Scheme 2). The octamer 12 derived from the minimally O-protected monomer 2 is insoluble, while the methoxymethyl- and triisopropysilyl-protected hexadecamer 54 prepared in twelve steps from the dimer 41 (Scheme 4), is readily soluble in a variety of solvents. O- and C-deprotection of 54 led in four steps and in 76% yield to the hexadecamer 63 (Schemes 5 and 6). There is only a small difference of spectroscopic properties between the protected octamer 50 and hexadecamer 54, and, similarly, between the unprotected octamer 64 and hexadecamer 63 (Fig. 3).

  DOI：

  10.1002/(sici)1522-2675(19990210)82:2<198::aid-hlca198>3.0.co;2-y